Synthesis of optically active amphiphilic tetrathiafulvalene derivatives

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3370-3379

  Gomar Nadal, Elba ^a   Rovira, Concepció ^a   Amabilino, David B ^a  

^a INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

Donor; Circular dichroism; Molecular electronics; Stereochemistry

Indexed keywords

2,3 BIS 2 CYANOETHYLTHIO 6,7 BIS 3,7 DIMETHYLOCT 6 ENYLTHIOTETRATHIAFULVALENE; 2,3 BIS 2 CYANOETHYLTHIO 6,7 BIS 3,7 DIMETHYLOCTYLTHIOTETRATHIAFULVALENE; 2,3 BIS 2 DODECYCLOXY PROPANYLTHIO) 6,7 BIS METHOXYCARBONYLTETRATHIAFULVALENE; 2,3 BIS 2 DODECYCLOXYPROPANYLTHIO 6 METHAOXYCARBONYLTETRATHIAFULVALENE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; OPTICAL ROTATION; PRIORITY JOURNAL; SPECTROSCOPY; SUBSTITUTION REACTION;

EID: 33644982351     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.056     Document Type: Article

References (70)

1. S. Decurtins, H.W. Schmalle, P. Schneuwly, J. Ensling, and P. Gütlich J. Am. Chem. Soc. 116 1994 9521 9528
2. S. Decurtins, H.W. Scmalle, R. Pellaux, R. Huber, P. Fischer, and B. Ouladdiaf Adv. Mater. 8 1996 647 651
3. G.L.J.A. Rikken, and E. Raupach Nature 390 1997 493 494
4. F. Pointillart, C. Train, M. Gruselle, F. Villain, H.W. Schmalle, D. Talbot, P. Gredin, S. Decurtins, and M. Verdaguer Chem. Mater. 16 2004 832 841
5. H. Imai, K. Inoue, K. Kikuchi, Y. Yoshida, M. Ito, T. Sunahara, and S. Onaka Angew. Chem., Int. Ed. 43 2004 5618 5621
6. E. Coronado, and J.R. Galan-Mascaros J. Mater. Chem. 15 2005 66 74
7. (g) Amabilino, D. B.; Veciana J. Top. Curr. Chem., in press.
8. M. Bryce Adv. Mater. 11 1999 11 23
9. M.R. Bryce J. Mater. Chem. 10 2000 589 598
10. J.L. Segura, and N. Martín Angew. Chem., Int. Ed. 40 2001 1372 1406
11. G. Schukat, and E. Fanghänel Sulfur Reports 24 2003 1 190
12. J.-I. Yamada T. Sugimoto TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalene 2004 Springer Berlin
13. A. Gorgues J. Phys. IV 114 2004 405 410
14. Chem. Rev. 2004 104 Special issue "Molecular Conductors" no. 11
15. M.A. Herranz, L. Sanchez, and N. Martin Phosphorus, Sulfur Silicon Relat. Elem. 180 2005 1133 1148
16. A.W.-W.A.O. Sarhan Tetrahedron 61 2005 3889 3932
17. M.B. Nielsen, C. Lomholt, and J. Becher Chem. Soc. Rev. 29 2000 153 164
18. T. Uemura, K. Naka, and Y. Chujo Adv. Polym. Sci. 167 2004 81 106
19. C.P. Collier, G. Mattersteig, E.W. Wong, Y. Luo, K. Beverly, J. Sampaio, F. Raymo, J.F. Stoddart, and J.R. Heath Science 289 2000 1172 1175
20. A.R. Pease, J.O. Jeppesen, J.F. Stoddart, Y. Luo, C.P. Collier, and J.R. Heath Acc. Chem. Res. 34 2001 433 444
21. J. Chen, M.A. Reed, D.W. Price, and J.M. Tour Appl. Phys. Lett. 78 2001 3735 3737
22. R.L. Carroll, and C.B. Gorman Angew. Chem., Int. Ed. 41 2002 4378 4400
23. R.M. Metzger Chem. Rev. 103 2003 3803 3834
24. P. Samori, and J.P. Rabe J. Phys.: Condens. Matter 14 2002 9955 9973
25. G. Maruccio, R. Cingolani, and R. Rinaldi J. Mater. Chem. 14 2004 542 554
26. E. Gomar-Nadal, G.K. Ramachandran, F. Chen, T. Burgin, C. Rovira, D.B. Amabilino, and S.M. Lindsay J. Phys. Chem. B 108 2004 7213 7218
27. M. Mas-Torrent, P. Hadley, S.T. Bromley, X. Ribas, J. Tarres, M. Mas, E. Molins, J. Veciana, and C. Rovira J. Am. Chem. Soc. 126 2004 8546 8553
28. A.H. Flood, J.F. Stoddart, D.W. Steuerman, and J.R. Heath Science 306 2004 2055 2056
29. N. Saygili, R.J. Brown, P. Day, R. Hoelzl, P. Kathirgamanathan, E.R. Mageean, T. Ozturk, M. Pilkington, M.M.B. Qayyum, S.S. Turner, L. Vorwerg, and J.D. Wallis Tetrahedron 2001 5015 5026
30. J.D. Wallis, and J.-P. Griffiths J. Mater. Chem. 15 2005 347 365
31. J.-P. Griffiths, H. Nie, R.J. Brown, P. Day, and J.D. Wallis Org. Biomol. Chem. 3 2005 2155 2166
32. A. Chesney, and M.R. Bryce Tetrahedron: Asymmetry 7 1996 3247 3254
33. C. Réthoré, M. Fourmigué, and N. Avarvari Chem. Commun. 2004 1384 1385
34. C. Réthoré, N. Avarvari, E. Canadell, P. Auban-Senzier, and M. Formigué J. Am. Chem. Soc. 127 2005 5748 5749
35. C. Réthoré, M. Fourmigué, and N. Avarvari Tetrahedron 61 2005 10935 10942
36. J.D. Wallis, A. Karrer, and J. Dunitz Helv. Chim. Acta 69 1986 69 70
37. T. Ozturk, C.R. Rice, and J.D. Wallis J. Mater. Chem. 5 1995 1553 1556
38. T. Ozturk, D.C. Povey, and J.D. Wallis Tetrahedron 50 1994 11205 11212
39. F. Leurquin, T. Ozturk, M. Pilkington, and J. Wallis J. Chem. Soc., Perkin Trans. 1 1997 3173 3177
40. G.A. Horley, T. Ozturk, F. Turksoy, and J. Wallis J. Chem. Soc., Perkin Trans. 1 1998 3225 3231
41. T. Ozturk, N. Saygili, S. Ozkara, M. Pilkington, C.R. Rice, D.A. Tranter, F. Turksoy, and J.D. Wallis J. Chem. Soc., Perkin Trans. 1 2001 407 414
42. P. Wu, G. Saito, K. Imaeda, Z. Shi, T. Mori, T. Enoki, and H. Inokuchi Chem. Lett. 1986 441 444
43. R. Andreu, J. Barberá, J. Garín, J. Orduna, J.-L. Serrano, T. Sierra, P. Leriche, M. Sallé, A. Riou, M. Jubault, and A. Gorgues J. Mater. Chem. 8 1998 881 887
44. P. Cea, J.I. Pardo, J.S. Urieta, M.C. Lopez, and F.M. Royo Electrochim. Acta 46 2000 589 597
45. M. Narita, and C.U. Pittman Synthesis 1976 489 514
46. M.R. Bryce Aldrichim. Acta 18 1985 73
47. A. Krief Tetrahedron 42 1986 1209 1259
48. D. Cowan, and A. Kini The Chemistry of Organic Selenium and Tellurium Compounds Vol. 2 1987 Wiley Chichester
49. K. Kobayashi, K. Kikuchi, T. Namiki, and I. Ikemoto Synth. Met. 19 1987 555 558
50. T. Mori, H. Inokuchi, and A.M. Kini Chem. Lett. 1990 1279 1282
51. O. Mitsunobu Synthesis 1981 1 28
52. M. Varasi, K.A.M. Walker, and M.L. Maddox J. Org. Chem. 52 1987 4235 4238
53. Hughes, D. L. In Organic Reactions (Eds. Paquette et al.), 1992 Vol. 42, pp 335-656.
54. R.-M. Olk, B. Olk, W. Dietzsch, R. Kirmse, and E. Hoyer Coord. Chem. Rev. 117 1992 99 131
55. T.K. Hansen, J. Becher, T. Jørgensen, K.S. Varma, R. Khedekar, and M.P. Cava Org. Synth. 73 1996 270 277
56. J. Lau, O. Simonsen, and J. Becher Synthesis 1995 521 526
57. T. Gajda Synthesis 1988 327 328
58. J.R. Dormoy Synthesis 1982 753 756
59. von. H. Loibner, and E. Zbiral Helv. Chim. Acta 59 1976 2017 2100
60. P. Rollin Tetrahedron Lett. 27 1986 4169 4170
61. N. Ruiz, and P. Rollin Tetrahedron Lett. 30 1989 1637 1640
62. K.B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, P. Mork, G.J. Kristensen, and J. Becher Synthesis 1996 407 418
63. P.G. Stevens J. Am. Chem. Soc. 54 1932 3732 3738
64. J. Barberá, R. Iglesias, J.L. Serrano, T. Sierra, M.R. de la Fuente, B. Palacios, M.A. Pérez-Jubindo, and J.T. Vázquez J. Am. Chem. Soc. 120 1998 2908 2918
65. G. Hilgetag, and A. Martini Preparative Organic Chemistry 1972 Wiley New York 214 231
66. R.O. Hutchins, D. Masilamani, and C.A. Maryanoff J. Org. Chem. 41 1976 1071 1073
67. J. Clayden, N. Greeves, S. Warren, and P. Wothers Organic Synthesis 2001 Oxford University Press New York 427
68. J. Sly, P. Kasák, E. Gomar-Nadal, C. Rovira, L. Górriz, P. Thordarson, D.B. Amabilino, A.E. Rowan, and R.J.M. Nolte Chem. Commun. 2005 1255 1257
69. P.R. Prag, J.D. Kilburn, M.C. Petty, C. Pearson, and T.G. Ryan Synthesis 1994 613 618
70. N. Svenstrup, K.M. Rasmussen, T. Kruse, and J. Becher Synthesis 1994 809 812